Fmoc-O-trityl-L-threonine is a protected threonine derivative in which the amino acid backbone is functionalized for peptide chemistry, featuring a threonine side chain with a β-hydroxyl group and a primary carboxyl group that is masked by protection. The molecule contains an Fmoc (9-fluorenylmethoxycarbonyl) group on the amino functionality and an O-trityl (trityl ether) protecting group on the side-chain hydroxyl, with the L stereochemical designation indicated in the product name. In synthesis, this orthogonally protected amino acid is employed as a building block for stepwise peptide assembly where the Fmoc group supports controlled N-deprotection and the trityl ether helps suppress side reactions from the unprotected β-hydroxyl during coupling and subsequent transformations.
CAT No: CP01920
CAS No:133180-01-5
Synonyms/Alias:Fmoc-Thr(Trt)-OH;133180-01-5;Fmoc-O-trityl-L-threonine;PubChem10043;SCHEMBL1738680;CTK3J8321;MolPort-006-701-289;ANW-43290;CF-485;FC1249;ZINC71788126;AKOS015895554;AM82254;RTR-004529;AK-81222;KB-52145;TR-004529;FT-0629904;ST24047305;ST51052975;B-7145;M03391;I06-1168
Fmoc-O-trityl-L-threonine is an Fmoc-protected threonine derivative in which the side-chain hydroxyl is masked as an O-trityl ether, preserving the L stereochemistry at the α-carbon while introducing a bulky, acid-labile protecting group on the functional handle. The molecule contains an Fmoc carbamate for N-protection, a free carboxyl functionality suitable for peptide coupling chemistry, and a secondary alcohol equivalent that is rendered non-nucleophilic by trityl caging. The combination of an orthogonally removable N-protecting group (Fmoc) and an O-protecting group (trityl) yields a controlled deprotection profile that supports stepwise construction of protected amino acid sequences. The pronounced steric demand of the trityl group can influence coupling efficiency and side-chain reactivity, making the compound a practical chiral intermediate for threonine-based peptide building block preparation and downstream functional transformations.
1. Peptide Synthesis
Fmoc-O-trityl-L-threonine is used as a threonine peptide building block in solid-phase peptide synthesis and related protected amino acid assembly workflows. The Fmoc carbamate enables standard N-terminal activation and coupling while the carboxyl group participates in amide bond formation to extend peptide chains. The O-trityl protection suppresses side-chain hydroxyl reactivity during chain elongation, reducing undesired esterification or crosslinking and supporting clean peptide growth. Stepwise deprotection strategies can reveal the threonine side-chain hydroxyl after peptide assembly, enabling subsequent phosphorylation-mimic chemistry, glycosylation, or further derivatization. The protected amino acid ester/acid functionality and orthogonal protecting-group design make it suitable for constructing threonine-rich sequences and peptide analogs where side-chain control is required.
2. Side-Chain Functionalization
Fmoc-O-trityl-L-threonine supports amino acid derivatization programs targeting controlled modification of the threonine side-chain hydroxyl. The O-trityl ether functions as a removable protecting group that can be selectively cleaved under conditions compatible with the Fmoc strategy, allowing timed exposure of the secondary alcohol for subsequent transformations. The revealed hydroxyl can then be used to generate phosphate mimics, engage in ether formation, or serve as a handle for conjugation chemistries that require site-specific reactivity. The retained L stereochemistry at the α-carbon helps maintain stereochemical fidelity in downstream peptidomimetics and biochemical probes. Side-chain functionalization using this chiral, protected intermediate aligns with amino acid chemistry workflows that require orthogonal protection and predictable reactivity control.
3. Chemical Biology Probes
Fmoc-O-trityl-L-threonine can be applied in chemical biology research where threonine-containing peptides or peptidomimetics are used as substrates, binding ligands, or labeling scaffolds. The protected hydroxyl and Fmoc-protected amine enable incorporation into defined sequences for generating molecular recognition tools with controlled functional group placement. Trityl masking prevents premature side-chain reactions during synthesis of peptide-based probes, supporting consistent probe composition for analytical characterization and structure-activity relationship studies. Deprotection and functionalization of the side-chain hydroxyl can be used to install handles for affinity tags, clickable groups, or phosphorylation-state analogs that mimic biochemical motifs. The compound's stereodefined amino acid framework and orthogonal protection scheme make it compatible with iterative probe construction and downstream biomolecule modification research.
4. Peptidomimetics And SAR
Fmoc-O-trityl-L-threonine is suitable for peptidomimetic construction and structure-activity relationship studies that require threonine stereocontrol and controlled side-chain chemistry. The Fmoc-protected nitrogen and carboxyl group allow formation of amide linkages that maintain a peptide-like backbone while enabling systematic variation of adjacent residues. The O-trityl group provides a stable, non-reactive side-chain during scaffold assembly, while later deprotection can unlock the hydroxyl for targeted substitutions that tune polarity, hydrogen-bonding, and conformational preferences. Incorporation of this protected threonine intermediate into analog libraries can support SAR workflows where side-chain functional diversity is introduced without compromising the chiral center. The compound thus functions as a practical chiral building block for generating threonine-modified molecular scaffolds in synthetic organic chemistry and applied medicinal chemistry research.
5. Pharmaceutical Intermediate Preparation
Fmoc-O-trityl-L-threonine can serve as a process-relevant protected amino acid intermediate for manufacturing routes that require controlled protection of both the amino group and threonine side-chain hydroxyl. The Fmoc carbamate provides a robust N-protecting strategy compatible with peptide coupling steps, while the trityl ether offers an acid-labile protection mode for orthogonal deprotection planning. The defined stereochemistry at the α-carbon supports reproducible downstream formation of threonine-containing intermediates used in peptide-based active ingredients, peptide fragments, or process intermediates for further functionalization. The bulky trityl group can also help manage side reactions during multi-step synthesis by temporarily suppressing hydroxyl nucleophilicity until the intended stage. This makes the compound applicable to fine chemical synthesis and pharmaceutical intermediate preparation where protecting-group logic and stepwise transformation control are central to scalable production planning.
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